Structure

Physi-Chem Properties

Molecular Weight:  810.44
Volume:  799.037
LogP:  2.586
LogD:  2.611
LogS:  -3.095
# Rotatable Bonds:  8
TPSA:  253.13
# H-Bond Aceptor:  15
# H-Bond Donor:  9
# Rings:  7
# Heavy Atoms:  15

MedChem Properties

QED Drug-Likeness Score:  0.1
Synthetic Accessibility Score:  5.916
Fsp3:  0.905
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.107
MDCK Permeability:  5.919460454606451e-05
Pgp-inhibitor:  0.924
Pgp-substrate:  0.029
Human Intestinal Absorption (HIA):  0.946
20% Bioavailability (F20%):  0.202
30% Bioavailability (F30%):  0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.044
Plasma Protein Binding (PPB):  85.37167358398438%
Volume Distribution (VD):  0.448
Pgp-substrate:  7.074894905090332%

ADMET: Metabolism

CYP1A2-inhibitor:  0.002
CYP1A2-substrate:  0.117
CYP2C19-inhibitor:  0.001
CYP2C19-substrate:  0.434
CYP2C9-inhibitor:  0.001
CYP2C9-substrate:  0.036
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.065
CYP3A4-inhibitor:  0.044
CYP3A4-substrate:  0.036

ADMET: Excretion

Clearance (CL):  0.835
Half-life (T1/2):  0.536

ADMET: Toxicity

hERG Blockers:  0.015
Human Hepatotoxicity (H-HT):  0.223
Drug-inuced Liver Injury (DILI):  0.019
AMES Toxicity:  0.116
Rat Oral Acute Toxicity:  0.106
Maximum Recommended Daily Dose:  0.146
Skin Sensitization:  0.012
Carcinogencity:  0.024
Eye Corrosion:  0.003
Eye Irritation:  0.009
Respiratory Toxicity:  0.505

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Data Type Select
General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC30397

Natural Product ID:  NPC30397
Common Name*:   3-O-Beta-D-Glucopyranosyl Quinovic Acid28-O-Beta-D-Glucopyranosyl Ester
IUPAC Name:   (1S,2R,4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-1,2,6b,9,9,12a-hexamethyl-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-6a-carboxylic acid
Synonyms:  
Standard InCHIKey:  LDCLXZSKVDYDBF-DTJUAWDLSA-N
Standard InCHI:  InChI=1S/C42H66O15/c1-19-9-14-41(37(53)57-35-33(50)31(48)29(46)23(18-44)55-35)15-16-42(36(51)52)21(27(41)20(19)2)7-8-25-39(5)12-11-26(38(3,4)24(39)10-13-40(25,42)6)56-34-32(49)30(47)28(45)22(17-43)54-34/h7,19-20,22-35,43-50H,8-18H2,1-6H3,(H,51,52)/t19-,20+,22-,23-,24+,25-,26+,27+,28-,29-,30+,31+,32-,33-,34+,35+,39+,40-,41+,42-/m1/s1
SMILES:  OC[C@H]1O[C@@H](O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3CC=C3[C@]2(CC[C@@]2([C@H]3[C@@H](C)[C@H](C)CC2)C(=O)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)C(=O)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL501302
PubChem CID:   14194010
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0002049] Terpene glycosides
          • [CHEMONTID:0001580] Triterpene glycosides
            • [CHEMONTID:0002358] Triterpene saponins

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO26547 Uncaria tomentosa Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[1919590]
NPO25311 Guettarda platypoda Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[2553871]
NPO26547 Uncaria tomentosa Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[2553871]
NPO26547 Uncaria tomentosa Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22560 Strychnos parvifolia Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26547 Uncaria tomentosa Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22560 Strychnos parvifolia Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26547 Uncaria tomentosa Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22560 Strychnos parvifolia Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22475.1 Brachylaena discolor var. rotundata Varieties Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22818 Acritopappus confertus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25311 Guettarda platypoda Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21220 Pulicaria uliginosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT165 Cell Line HeLa Homo sapiens MNCC = 100.0 ug ml-1 PMID[449562]
NPT1044 Individual Protein DNA topoisomerase II alpha Homo sapiens IC50 > 250000.0 nM PMID[449563]
NPT143 Individual Protein DNA topoisomerase I Homo sapiens IC50 > 250000.0 nM PMID[449563]
NPT2516 Organism Vesicular stomatitis Indiana virus Vesicular stomatitis Indiana virus MIC50 = 40000.0 nM PMID[449562]
NPT27 Others Unspecified TC50 = 150.0 ug ml-1 PMID[449562]
NPT2517 Organism Human rhinovirus 1B Human rhinovirus 1B Activity = 50.0 % PMID[449562]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC30397 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC473481
1.0 High Similarity NPC211798
1.0 High Similarity NPC108748
1.0 High Similarity NPC235841
1.0 High Similarity NPC297208
0.9903 High Similarity NPC256798
0.9903 High Similarity NPC128925
0.9902 High Similarity NPC474589
0.9902 High Similarity NPC29069
0.9902 High Similarity NPC56713
0.9902 High Similarity NPC475296
0.9902 High Similarity NPC279554
0.9902 High Similarity NPC127056
0.9902 High Similarity NPC174679
0.9902 High Similarity NPC90856
0.9902 High Similarity NPC59804
0.9902 High Similarity NPC270667
0.9902 High Similarity NPC164194
0.9902 High Similarity NPC136877
0.9902 High Similarity NPC274507
0.9808 High Similarity NPC138334
0.9808 High Similarity NPC204458
0.9808 High Similarity NPC258885
0.9808 High Similarity NPC189884
0.9808 High Similarity NPC124296
0.9808 High Similarity NPC47063
0.9806 High Similarity NPC164419
0.9806 High Similarity NPC179434
0.9806 High Similarity NPC191763
0.9804 High Similarity NPC306746
0.9804 High Similarity NPC167383
0.9804 High Similarity NPC237503
0.9804 High Similarity NPC57362
0.9804 High Similarity NPC204407
0.9712 High Similarity NPC139044
0.9712 High Similarity NPC46388
0.9712 High Similarity NPC102439
0.9712 High Similarity NPC1046
0.9712 High Similarity NPC104400
0.9712 High Similarity NPC37739
0.9712 High Similarity NPC10320
0.9712 High Similarity NPC324875
0.9712 High Similarity NPC276093
0.9712 High Similarity NPC257468
0.9712 High Similarity NPC104071
0.9712 High Similarity NPC475504
0.9712 High Similarity NPC469946
0.9712 High Similarity NPC139894
0.9712 High Similarity NPC475516
0.9712 High Similarity NPC471383
0.9712 High Similarity NPC101744
0.9712 High Similarity NPC473373
0.9712 High Similarity NPC116794
0.9712 High Similarity NPC109079
0.9712 High Similarity NPC79718
0.9712 High Similarity NPC80843
0.9712 High Similarity NPC292677
0.9712 High Similarity NPC473383
0.9709 High Similarity NPC476880
0.9709 High Similarity NPC476883
0.9709 High Similarity NPC269095
0.9709 High Similarity NPC110139
0.9709 High Similarity NPC476884
0.9709 High Similarity NPC476887
0.9709 High Similarity NPC476882
0.9709 High Similarity NPC199457
0.9709 High Similarity NPC102914
0.9709 High Similarity NPC7870
0.9709 High Similarity NPC476881
0.9709 High Similarity NPC476885
0.9709 High Similarity NPC75747
0.9709 High Similarity NPC68419
0.9709 High Similarity NPC108709
0.9709 High Similarity NPC78046
0.9709 High Similarity NPC476886
0.9706 High Similarity NPC177246
0.9706 High Similarity NPC476123
0.9706 High Similarity NPC284807
0.9706 High Similarity NPC28198
0.9623 High Similarity NPC160415
0.9623 High Similarity NPC58448
0.9623 High Similarity NPC471384
0.9623 High Similarity NPC161674
0.9619 High Similarity NPC219180
0.9619 High Similarity NPC163183
0.9619 High Similarity NPC251263
0.9619 High Similarity NPC155410
0.9619 High Similarity NPC114287
0.9619 High Similarity NPC238935
0.9619 High Similarity NPC269315
0.9619 High Similarity NPC96641
0.9619 High Similarity NPC241909
0.9619 High Similarity NPC295823
0.9619 High Similarity NPC475467
0.9619 High Similarity NPC473343
0.9619 High Similarity NPC166422
0.9619 High Similarity NPC151543
0.9619 High Similarity NPC133818
0.9619 High Similarity NPC473826
0.9619 High Similarity NPC475287
0.9619 High Similarity NPC73318
0.9619 High Similarity NPC192600
0.9619 High Similarity NPC174720
0.9619 High Similarity NPC271138
0.9619 High Similarity NPC475208
0.9619 High Similarity NPC114304
0.9619 High Similarity NPC309714
0.9619 High Similarity NPC323341
0.9619 High Similarity NPC150400
0.9619 High Similarity NPC46665
0.9619 High Similarity NPC134835
0.9615 High Similarity NPC31839
0.9612 High Similarity NPC137917
0.9612 High Similarity NPC127853
0.9608 High Similarity NPC473538
0.9608 High Similarity NPC283849
0.9533 High Similarity NPC148417
0.9533 High Similarity NPC68175
0.9533 High Similarity NPC136768
0.9533 High Similarity NPC110633
0.9528 High Similarity NPC475633
0.9528 High Similarity NPC293330
0.9528 High Similarity NPC475140
0.9528 High Similarity NPC67857
0.9528 High Similarity NPC473714
0.9528 High Similarity NPC475486
0.9528 High Similarity NPC65105
0.9528 High Similarity NPC76972
0.9528 High Similarity NPC204414
0.9528 High Similarity NPC123199
0.9528 High Similarity NPC70809
0.9528 High Similarity NPC100639
0.9528 High Similarity NPC41061
0.9528 High Similarity NPC469782
0.9528 High Similarity NPC54636
0.9528 High Similarity NPC164389
0.9528 High Similarity NPC119592
0.9528 High Similarity NPC57484
0.9528 High Similarity NPC4328
0.9528 High Similarity NPC471385
0.9528 High Similarity NPC161717
0.9528 High Similarity NPC476068
0.9528 High Similarity NPC60557
0.9528 High Similarity NPC298034
0.9528 High Similarity NPC202828
0.9528 High Similarity NPC224381
0.9528 High Similarity NPC305981
0.9528 High Similarity NPC261506
0.9528 High Similarity NPC79643
0.9528 High Similarity NPC227551
0.9528 High Similarity NPC43550
0.9528 High Similarity NPC236638
0.9528 High Similarity NPC71065
0.9528 High Similarity NPC250247
0.9528 High Similarity NPC471550
0.9528 High Similarity NPC309907
0.9528 High Similarity NPC475160
0.9528 High Similarity NPC294453
0.9524 High Similarity NPC195132
0.9524 High Similarity NPC48249
0.9524 High Similarity NPC161434
0.9524 High Similarity NPC471967
0.9519 High Similarity NPC220984
0.9519 High Similarity NPC242611
0.9515 High Similarity NPC285576
0.951 High Similarity NPC475611
0.9444 High Similarity NPC36831
0.9439 High Similarity NPC476992
0.9439 High Similarity NPC75287
0.9439 High Similarity NPC288205
0.9439 High Similarity NPC26626
0.9439 High Similarity NPC37134
0.9439 High Similarity NPC305267
0.9439 High Similarity NPC51465
0.9439 High Similarity NPC291903
0.9429 High Similarity NPC190837
0.9412 High Similarity NPC173583
0.9352 High Similarity NPC473824
0.9352 High Similarity NPC33012
0.9352 High Similarity NPC85154
0.9352 High Similarity NPC309223
0.9352 High Similarity NPC185466
0.9352 High Similarity NPC323359
0.9352 High Similarity NPC470876
0.9352 High Similarity NPC69811
0.9352 High Similarity NPC475119
0.9352 High Similarity NPC473452
0.9352 High Similarity NPC286457
0.9352 High Similarity NPC475514
0.9352 High Similarity NPC8524
0.9352 High Similarity NPC300419
0.9352 High Similarity NPC191827
0.9352 High Similarity NPC102505
0.9352 High Similarity NPC471547
0.9352 High Similarity NPC220160
0.9352 High Similarity NPC123522
0.9352 High Similarity NPC104137
0.9352 High Similarity NPC473405
0.9352 High Similarity NPC475209
0.934 High Similarity NPC212968

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC30397 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.9 High Similarity NPD8295 Clinical (unspecified phase)
0.8879 High Similarity NPD8132 Clinical (unspecified phase)
0.886 High Similarity NPD8328 Phase 3
0.8393 Intermediate Similarity NPD8133 Approved
0.8182 Intermediate Similarity NPD6412 Phase 2
0.8108 Intermediate Similarity NPD6686 Approved
0.8051 Intermediate Similarity NPD8033 Approved
0.8 Intermediate Similarity NPD7748 Approved
0.7966 Intermediate Similarity NPD8377 Approved
0.7966 Intermediate Similarity NPD8294 Approved
0.7944 Intermediate Similarity NPD7902 Approved
0.7934 Intermediate Similarity NPD7507 Approved
0.7899 Intermediate Similarity NPD8296 Approved
0.7899 Intermediate Similarity NPD8380 Approved
0.7899 Intermediate Similarity NPD8378 Approved
0.7899 Intermediate Similarity NPD8379 Approved
0.7899 Intermediate Similarity NPD8335 Approved
0.781 Intermediate Similarity NPD7515 Phase 2
0.775 Intermediate Similarity NPD8516 Approved
0.775 Intermediate Similarity NPD8515 Approved
0.775 Intermediate Similarity NPD8513 Phase 3
0.775 Intermediate Similarity NPD8517 Approved
0.7742 Intermediate Similarity NPD7319 Approved
0.7664 Intermediate Similarity NPD7900 Approved
0.7664 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7661 Intermediate Similarity NPD7736 Approved
0.7647 Intermediate Similarity NPD7328 Approved
0.7647 Intermediate Similarity NPD7327 Approved
0.7583 Intermediate Similarity NPD7516 Approved
0.7459 Intermediate Similarity NPD7503 Approved
0.744 Intermediate Similarity NPD8293 Discontinued
0.7368 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7315 Intermediate Similarity NPD8034 Phase 2
0.7315 Intermediate Similarity NPD8035 Phase 2
0.7288 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7258 Intermediate Similarity NPD6370 Approved
0.7248 Intermediate Similarity NPD6399 Phase 3
0.7232 Intermediate Similarity NPD7638 Approved
0.7227 Intermediate Similarity NPD8297 Approved
0.7227 Intermediate Similarity NPD6882 Approved
0.7168 Intermediate Similarity NPD7640 Approved
0.7168 Intermediate Similarity NPD7639 Approved
0.7157 Intermediate Similarity NPD7645 Phase 2
0.7143 Intermediate Similarity NPD7492 Approved
0.7131 Intermediate Similarity NPD6009 Approved
0.7119 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD6054 Approved
0.7097 Intermediate Similarity NPD6319 Approved
0.7097 Intermediate Similarity NPD6059 Approved
0.7087 Intermediate Similarity NPD6616 Approved
0.7075 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD6067 Discontinued
0.7034 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7031 Intermediate Similarity NPD7078 Approved
0.7025 Intermediate Similarity NPD4632 Approved
0.7009 Intermediate Similarity NPD5739 Approved
0.7009 Intermediate Similarity NPD6675 Approved
0.7009 Intermediate Similarity NPD6402 Approved
0.7009 Intermediate Similarity NPD7128 Approved
0.7 Intermediate Similarity NPD6411 Approved
0.6992 Remote Similarity NPD7115 Discovery
0.6975 Remote Similarity NPD6372 Approved
0.6975 Remote Similarity NPD6373 Approved
0.6937 Remote Similarity NPD8171 Discontinued
0.6917 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6909 Remote Similarity NPD46 Approved
0.6909 Remote Similarity NPD6698 Approved
0.6905 Remote Similarity NPD6015 Approved
0.6905 Remote Similarity NPD6016 Approved
0.6899 Remote Similarity NPD8074 Phase 3
0.6891 Remote Similarity NPD6881 Approved
0.6891 Remote Similarity NPD6899 Approved
0.6891 Remote Similarity NPD7320 Approved
0.686 Remote Similarity NPD6650 Approved
0.686 Remote Similarity NPD8130 Phase 1
0.686 Remote Similarity NPD6649 Approved
0.685 Remote Similarity NPD5988 Approved
0.6822 Remote Similarity NPD4786 Approved
0.6818 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6818 Remote Similarity NPD6101 Approved
0.6807 Remote Similarity NPD5701 Approved
0.6807 Remote Similarity NPD5697 Approved
0.6792 Remote Similarity NPD3667 Approved
0.6783 Remote Similarity NPD4225 Approved
0.6777 Remote Similarity NPD7102 Approved
0.6777 Remote Similarity NPD7290 Approved
0.6777 Remote Similarity NPD6883 Approved
0.6727 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6723 Remote Similarity NPD6008 Approved
0.6721 Remote Similarity NPD6869 Approved
0.6721 Remote Similarity NPD6847 Approved
0.6721 Remote Similarity NPD6617 Approved
0.6697 Remote Similarity NPD3618 Phase 1
0.6696 Remote Similarity NPD6083 Phase 2
0.6696 Remote Similarity NPD6084 Phase 2
0.6696 Remote Similarity NPD7983 Approved
0.6694 Remote Similarity NPD6013 Approved
0.6694 Remote Similarity NPD6014 Approved
0.6694 Remote Similarity NPD6012 Approved
0.6667 Remote Similarity NPD7604 Phase 2
0.6667 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5328 Approved
0.6667 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6642 Remote Similarity NPD8449 Approved
0.6641 Remote Similarity NPD5983 Phase 2
0.6638 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6637 Remote Similarity NPD5779 Approved
0.6637 Remote Similarity NPD5778 Approved
0.6636 Remote Similarity NPD3573 Approved
0.6612 Remote Similarity NPD6011 Approved
0.661 Remote Similarity NPD7632 Discontinued
0.6593 Remote Similarity NPD8450 Suspended
0.6591 Remote Similarity NPD6033 Approved
0.6585 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6574 Remote Similarity NPD3670 Clinical (unspecified phase)
0.6574 Remote Similarity NPD3669 Approved
0.6565 Remote Similarity NPD6336 Discontinued
0.6552 Remote Similarity NPD4755 Approved
0.6549 Remote Similarity NPD6079 Approved
0.6545 Remote Similarity NPD7334 Approved
0.6545 Remote Similarity NPD6409 Approved
0.6545 Remote Similarity NPD7521 Approved
0.6545 Remote Similarity NPD6684 Approved
0.6545 Remote Similarity NPD5330 Approved
0.6545 Remote Similarity NPD7146 Approved
0.6512 Remote Similarity NPD6921 Approved
0.6508 Remote Similarity NPD6940 Discontinued
0.6504 Remote Similarity NPD4634 Approved
0.6491 Remote Similarity NPD4202 Approved
0.6457 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6449 Remote Similarity NPD7525 Registered
0.6441 Remote Similarity NPD4696 Approved
0.6441 Remote Similarity NPD5286 Approved
0.6441 Remote Similarity NPD4700 Approved
0.6441 Remote Similarity NPD5285 Approved
0.6429 Remote Similarity NPD5737 Approved
0.6429 Remote Similarity NPD6903 Approved
0.6429 Remote Similarity NPD6672 Approved
0.6415 Remote Similarity NPD6114 Approved
0.6415 Remote Similarity NPD6697 Approved
0.6415 Remote Similarity NPD6115 Approved
0.6415 Remote Similarity NPD6118 Approved
0.6389 Remote Similarity NPD1779 Approved
0.6389 Remote Similarity NPD1780 Approved
0.6389 Remote Similarity NPD7625 Phase 1
0.6387 Remote Similarity NPD5344 Discontinued
0.6379 Remote Similarity NPD5695 Phase 3
0.6378 Remote Similarity NPD6274 Approved
0.6364 Remote Similarity NPD8340 Approved
0.6364 Remote Similarity NPD8299 Approved
0.6364 Remote Similarity NPD8341 Approved
0.6364 Remote Similarity NPD3666 Approved
0.6364 Remote Similarity NPD3668 Phase 3
0.6364 Remote Similarity NPD3665 Phase 1
0.6364 Remote Similarity NPD3133 Approved
0.6364 Remote Similarity NPD8342 Approved
0.6357 Remote Similarity NPD7101 Approved
0.6357 Remote Similarity NPD7100 Approved
0.6356 Remote Similarity NPD5696 Approved
0.6343 Remote Similarity NPD8336 Approved
0.6343 Remote Similarity NPD8337 Approved
0.6333 Remote Similarity NPD5226 Approved
0.6333 Remote Similarity NPD4633 Approved
0.6333 Remote Similarity NPD5224 Approved
0.6333 Remote Similarity NPD5225 Approved
0.6333 Remote Similarity NPD5211 Phase 2
0.6325 Remote Similarity NPD4697 Phase 3
0.6325 Remote Similarity NPD5221 Approved
0.6325 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6325 Remote Similarity NPD5222 Approved
0.6325 Remote Similarity NPD7839 Suspended
0.6321 Remote Similarity NPD6116 Phase 1
0.6316 Remote Similarity NPD8451 Approved
0.6316 Remote Similarity NPD7838 Discovery
0.6311 Remote Similarity NPD4767 Approved
0.6311 Remote Similarity NPD4768 Approved
0.6288 Remote Similarity NPD7830 Approved
0.6288 Remote Similarity NPD7829 Approved
0.6281 Remote Similarity NPD5175 Approved
0.6281 Remote Similarity NPD5174 Approved
0.6279 Remote Similarity NPD7641 Discontinued
0.6279 Remote Similarity NPD6335 Approved
0.6271 Remote Similarity NPD5173 Approved
0.627 Remote Similarity NPD6053 Discontinued
0.6269 Remote Similarity NPD8448 Approved
0.6261 Remote Similarity NPD7637 Suspended
0.626 Remote Similarity NPD8274 Clinical (unspecified phase)
0.626 Remote Similarity NPD6909 Approved
0.626 Remote Similarity NPD6908 Approved
0.625 Remote Similarity NPD8391 Approved
0.625 Remote Similarity NPD5223 Approved
0.625 Remote Similarity NPD8392 Approved
0.625 Remote Similarity NPD8390 Approved
0.625 Remote Similarity NPD6868 Approved
0.6239 Remote Similarity NPD6356 Clinical (unspecified phase)
0.623 Remote Similarity NPD5141 Approved
0.6228 Remote Similarity NPD4753 Phase 2
0.6226 Remote Similarity NPD6117 Approved
0.6212 Remote Similarity NPD8080 Discontinued
0.621 Remote Similarity NPD4730 Approved

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data